TWI626245B - D-阿洛酮糖結晶及其製造方法 - Google Patents
D-阿洛酮糖結晶及其製造方法 Download PDFInfo
- Publication number
- TWI626245B TWI626245B TW104134146A TW104134146A TWI626245B TW I626245 B TWI626245 B TW I626245B TW 104134146 A TW104134146 A TW 104134146A TW 104134146 A TW104134146 A TW 104134146A TW I626245 B TWI626245 B TW I626245B
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- Prior art keywords
- psicose
- purity
- solution
- crystals
- grain size
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- BJHIKXHVCXFQLS-PUFIMZNGSA-N D-psicose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO BJHIKXHVCXFQLS-PUFIMZNGSA-N 0.000 title claims abstract description 189
- 239000013078 crystal Substances 0.000 title claims abstract description 101
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000012535 impurity Substances 0.000 claims abstract description 7
- 235000021551 crystal sugar Nutrition 0.000 claims abstract description 5
- 235000000346 sugar Nutrition 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 24
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003456 ion exchange resin Substances 0.000 claims description 14
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 14
- 238000004587 chromatography analysis Methods 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 238000011033 desalting Methods 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 238000004042 decolorization Methods 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 claims 1
- 235000009508 confectionery Nutrition 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 abstract description 69
- 230000008025 crystallization Effects 0.000 abstract description 61
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 208000007976 Ketosis Diseases 0.000 abstract 1
- 150000002584 ketoses Chemical class 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 11
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000000926 separation method Methods 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000003957 anion exchange resin Substances 0.000 description 5
- 239000003729 cation exchange resin Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 230000006911 nucleation Effects 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000186216 Corynebacterium Species 0.000 description 2
- 241000186226 Corynebacterium glutamicum Species 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 150000000837 D-psicose derivatives Chemical class 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000001822 immobilized cell Anatomy 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011268 mixed slurry Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- -1 sucrose Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000012610 weak anion exchange resin Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
- B01D15/1814—Recycling of the fraction to be distributed
- B01D15/1821—Simulated moving beds
- B01D15/185—Simulated moving beds characterised by the components to be separated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction, e.g. ion-exchange, ion-pair, ion-suppression or ion-exclusion
- B01D15/361—Ion-exchange
- B01D15/363—Anion-exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
- B01D9/0013—Crystallisation cooling by heat exchange by indirect heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0036—Crystallisation on to a bed of product crystals; Seeding
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Thermal Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Analytical Chemistry (AREA)
- Sustainable Development (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ??10-2014-0141678 | 2014-10-20 | ||
| KR1020140141678A KR101749527B1 (ko) | 2014-10-20 | 2014-10-20 | D-사이코스 결정을 제조하는 방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201619177A TW201619177A (zh) | 2016-06-01 |
| TWI626245B true TWI626245B (zh) | 2018-06-11 |
Family
ID=55761091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW104134146A TWI626245B (zh) | 2014-10-20 | 2015-10-19 | D-阿洛酮糖結晶及其製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10246476B2 (es) |
| EP (1) | EP3210478B1 (es) |
| JP (1) | JP6413024B2 (es) |
| KR (1) | KR101749527B1 (es) |
| CN (1) | CN106852145B (es) |
| AR (1) | AR102354A1 (es) |
| ES (1) | ES2841357T3 (es) |
| PL (1) | PL3210478T3 (es) |
| TW (1) | TWI626245B (es) |
| WO (1) | WO2016064087A1 (es) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101723007B1 (ko) * | 2016-02-29 | 2017-04-04 | 씨제이제일제당(주) | 고순도 d-사이코스를 제조하는 방법 |
| TW201815814A (zh) | 2016-10-28 | 2018-05-01 | 美商泰特及賴爾材料美國有限責任公司 | 阿洛酮糖晶體、含此晶體的消費品及母液、以及其製備方法 |
| KR102072695B1 (ko) * | 2016-12-08 | 2020-03-02 | 주식회사 삼양사 | 재순환을 이용한 사이코스의 제조방법 및 장치 |
| KR102065155B1 (ko) | 2016-12-08 | 2020-02-11 | 주식회사 삼양사 | 사이코스의 제조방법 |
| KR102004941B1 (ko) * | 2016-12-08 | 2019-07-29 | 주식회사 삼양사 | 효율적인 사이코스의 제조 방법 |
| KR101988441B1 (ko) | 2016-12-27 | 2019-06-12 | 주식회사 삼양사 | 알룰로스의 정제 방법 |
| FR3061415B1 (fr) * | 2017-01-05 | 2021-07-16 | Roquette Freres | Sirops non cristallisables de d-allulose |
| FR3061414B1 (fr) | 2017-01-05 | 2021-07-16 | Roquette Freres | Sirops cristallisables de d-allulose |
| FR3061413B1 (fr) * | 2017-01-05 | 2021-08-27 | Roquette Freres | Procede de fabrication de cristaux de d-allulose |
| KR102004940B1 (ko) | 2017-06-30 | 2019-07-29 | 주식회사 삼양사 | 감미료 알룰로스를 제조하는 방법 |
| KR101988442B1 (ko) * | 2017-06-30 | 2019-06-12 | 주식회사 삼양사 | 결정형 기능성 감미료 |
| WO2019004554A1 (ko) * | 2017-06-30 | 2019-01-03 | 주식회사 삼양사 | 결정형 기능성 감미료의 제조방법 |
| KR102016701B1 (ko) * | 2017-06-30 | 2019-09-06 | 주식회사 삼양사 | 결정형 기능성 감미료의 제조방법 |
| MX2020008430A (es) | 2018-02-12 | 2020-12-10 | Samyang Corp | Metodo para producir edulcorante cristalino funcional. |
| KR102055695B1 (ko) * | 2018-05-25 | 2020-01-03 | 대상 주식회사 | D-알로오스 결정을 제조하는 방법 |
| CN108866247A (zh) * | 2018-09-18 | 2018-11-23 | 上海立足生物科技有限公司 | 连续大规模分离制备d-阿洛酮糖的方法和设备 |
| KR102439295B1 (ko) * | 2018-11-30 | 2022-09-02 | 씨제이제일제당 주식회사 | D-사이코스 결정 및 이의 제조 방법 |
| CN109748940A (zh) * | 2018-12-04 | 2019-05-14 | 吉林中粮生化有限公司 | 一种从乙醇溶液中结晶阿洛酮糖的方法 |
| DE102018131131B4 (de) | 2018-12-06 | 2025-10-16 | Bma Braunschweigische Maschinenbauanstalt Gmbh | Kontinuierliches Verfahren zur Gewinnung eines kristallinen Monosaccharides |
| KR102091774B1 (ko) | 2018-12-13 | 2020-03-20 | 씨제이제일제당 (주) | 알룰로스를 유효성분으로 포함하는 피부 미백용 조성물 |
| CN110627847B (zh) * | 2019-09-17 | 2023-06-13 | 山东百龙创园生物科技股份有限公司 | 一种阿洛酮糖晶体的制备方法 |
| CN110872332B (zh) * | 2019-10-24 | 2023-03-24 | 翁源广业清怡食品科技有限公司 | 一种阿洛酮糖的结晶工艺 |
| CN110951806B (zh) * | 2019-12-24 | 2023-01-10 | 山东百龙创园生物科技股份有限公司 | 一种含有d-阿洛酮糖的结晶组合物的制备工艺 |
| EP3865496A1 (de) * | 2020-02-12 | 2021-08-18 | Savanna Ingredients GmbH | Verfahren zur herstellung farbloser kohlenhydrate |
| US20230159579A1 (en) | 2020-05-27 | 2023-05-25 | Savanna Ingredients Gmbh | Crystallization of allulose under reduced pressure |
| KR20230062627A (ko) | 2020-09-07 | 2023-05-09 | 사바나 인그리디언트 게엠베하 | 고형 알룰로오스 조성물의 제조를 위한 압출 공정 |
| EP4000419A1 (de) | 2020-11-23 | 2022-05-25 | Savanna Ingredients GmbH | Trocknung von allulosekristallen |
| CN112574263B (zh) * | 2020-12-04 | 2021-12-07 | 山东百龙创园生物科技股份有限公司 | 一种阿洛酮糖结晶的制备方法 |
| CN115974939B (zh) * | 2021-10-15 | 2025-11-14 | 吉林中粮生化有限公司 | D-阿洛酮糖结晶的方法 |
| CN115974941B (zh) * | 2021-10-15 | 2025-11-14 | 吉林中粮生化有限公司 | 制备d-阿洛酮糖晶体的方法 |
| CN114085768B (zh) * | 2021-11-11 | 2023-07-25 | 河南飞天生物科技股份有限公司 | 一种用于生产阿洛酮糖的提纯装置及提纯方法 |
| CN116178460B (zh) * | 2021-11-26 | 2025-07-11 | 中粮营养健康研究院有限公司 | D-阿洛酮糖结晶的方法 |
| CN114868898A (zh) * | 2022-03-01 | 2022-08-09 | 新拓洋生物工程有限公司 | 一种含阿洛酮糖的甜味剂组合物及制备方法 |
| CN114456215A (zh) * | 2022-03-04 | 2022-05-10 | 河南中大恒源生物科技股份有限公司 | 一种d-阿洛酮糖晶体及其制备方法 |
| KR20240008136A (ko) | 2022-07-11 | 2024-01-18 | 대상 주식회사 | D-알룰로스 결정 제조방법 |
| WO2024047121A1 (en) | 2022-09-01 | 2024-03-07 | Savanna Ingredients Gmbh | Process for the preparation of a particulate allulose composition |
| CN116284166B (zh) * | 2022-09-08 | 2025-03-07 | 陕西省生物农业研究所 | 一种从糖浆中回收d-阿洛酮糖结晶的方法 |
| WO2025153524A1 (en) | 2024-01-16 | 2025-07-24 | Savanna Ingredients Gmbh | Process for the synthesis and purification of allulose |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250157A (zh) * | 2010-03-26 | 2011-11-23 | Cj第一制糖株式会社 | 制造d-阿洛酮糖晶体的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883365A (en) | 1972-01-04 | 1975-05-13 | Suomen Sokeri Oy | PH adjustment in fructose crystallization for increased yield |
| JPS491741A (es) | 1972-04-04 | 1974-01-09 | ||
| GB1456260A (en) | 1974-01-28 | 1976-11-24 | Suomen Sokeri Oy | Method for crystallization of fructose from water solution |
| US4133375A (en) | 1977-01-28 | 1979-01-09 | Unice Machine Company | Vertical heat exchanger |
| JP4627841B2 (ja) | 2000-06-08 | 2011-02-09 | 国立大学法人 香川大学 | プシコースの分離方法 |
| FI20010977A7 (fi) * | 2001-05-09 | 2002-11-10 | Danisco Sweeteners Oy | Kromatografinen erotusmenetelmä |
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| EP1860195B1 (en) | 2005-03-04 | 2018-01-03 | National University Corporation Kagawa University | Complex crystalline sugar comprising d-psicose and d-allose and process for production of the same |
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| KR20090118465A (ko) | 2008-05-14 | 2009-11-18 | 김주봉 | 장뇌삼 추출물을 유효성분으로 포함하는 뇌질환의 예방 및치료용 조성물 |
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2014
- 2014-10-20 KR KR1020140141678A patent/KR101749527B1/ko active Active
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2015
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- 2015-09-08 WO PCT/KR2015/009449 patent/WO2016064087A1/ko not_active Ceased
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Patent Citations (1)
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|---|---|---|---|---|
| CN102250157A (zh) * | 2010-03-26 | 2011-11-23 | Cj第一制糖株式会社 | 制造d-阿洛酮糖晶体的方法 |
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| EP3210478A4 (en) | 2018-07-18 |
| TW201619177A (zh) | 2016-06-01 |
| EP3210478B1 (en) | 2020-10-28 |
| US10246476B2 (en) | 2019-04-02 |
| AR102354A1 (es) | 2017-02-22 |
| EP3210478A1 (en) | 2017-08-30 |
| JP6413024B2 (ja) | 2018-10-24 |
| CN106852145B (zh) | 2020-03-20 |
| JP2017532382A (ja) | 2017-11-02 |
| PL3210478T3 (pl) | 2021-06-14 |
| CN106852145A (zh) | 2017-06-13 |
| ES2841357T3 (es) | 2021-07-08 |
| KR20160046143A (ko) | 2016-04-28 |
| US20170313734A1 (en) | 2017-11-02 |
| WO2016064087A1 (ko) | 2016-04-28 |
| KR101749527B1 (ko) | 2017-06-21 |
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